α-Stabilized phosphoylides as versatile multifunctional ligands

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 23, 1999, Pages 4111-4122

  Navarro, Rafael ^a   Urriolabeitia, Esteban P ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748810552     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906116i     Document Type: Review

References (96)

1. (a) E. Vedejs, Science, 1980, 207, 42;
2. (b) G. Wittig, Science, 1980, 210, 600 (reprint of the Nobel lecture).
3. (a) A. W. Johnson, Ylid Chemistry, Academic Press, New York, 1966;
4. (b) H. Schmidbaur, Acc. Chem. Res., 1975, 8, 62.
5. W. C. Kaska, Coord. Chem. Rev., 1983, 48, 1.
6. H. Schmidbaur, Angew. Chem., Int. Ed. Engl., 1983, 22, 907.
7. A. Laguna and M. Laguna, J. Organomet. Chem., 1990, 394, 743.
8. D. Steinborn, Angew. Chem., Int. Ed. Engl., 1992, 31, 401.
9. A. W. Johnson, W. C. Kaska, K. A. O. Starzewski and D. A. Dixon, Ylides and Imines of Phosphorus, John Wiley & Sons, New York, 1993, chapter 14 and references therein.
10. U. Belluco, R. A. Michelin, M. Mozzon, R. Bertani, G. Facchin, L. Zanotto and L. Pandolfo, J. Organomet. Chem., 1998, 557, 37.
11. M. P. Doyle, Comprehensive Organometallic Chemistry II, Editors E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon Press, Oxford, 1995, Vol. 12, p. 421.
12. O. I. Kolodiazhnyi, Tetrahedron, 1996, 52, 1855.
13. E. J. Coyne and D. G. Gilheany, Comprehensive Organic Functional Group Transformations, Editors A. R. Katritzky, O. Meth-Cohn and C. W. Rees, Pergamon Press, Oxford, 1995, Vol. 3, pp. 492-500.
14. H. J. Bestmann and R. Zimmerman, Comprehensive Organic Synthesis, Editor B. M. Trost, Pergamon Press, Oxford, 1991, Vol. 6, pp. 171-198.
15. (a) A. Padwa and S. F. Hornbuckle, Chem. Rev., 1991, 91, 263 (sulfur, nitrogen and ylides others than phosphorus);
16. (b) O. I. Kolodiazhnyi, Phosphorus Ylides, Chemistry and Application in Organic Synthesis, Wiley-VCH Verlag GmbH, Weinheim, 1999.
17. D. J. Burton, Z. Y. Yang and W. Qin, Chem. Rev., 1996, 96, 1641.
18. H. J. Cristau, Chem. Rev., 1994, 94, 1299.
19. See, for instance, those dedicated to ylide complexes of palladium, platinum and gold in the series: Comprehensive Organometallic Chemistry II, Editors E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon Press, Oxford, 1995;
20. (Pd) A. J. Canty, Comprehensive Organometallic Chemistry II, Vol. 9, pp. 227-230;
21. (Pt) G. K. Anderson, Comprehensive Organometallic Chemistry II, Vol. 9, pp. 495-496;
22. (Au) A. Grohmann and H. Schmidbaur, Comprehensive Organometallic Chemistry II, Vol. 3, pp. 12-31.
23. (a) H. Nishiyama, K. Itoh and Y. Ishii, J. Organomet. Chem., 1975, 87, 129;
24. (b) R. Usón, J. Forniés, R. Navarro, P. Espinet and C. Mendívil, J. Organomet. Chem., 1985, 290, 125.
25. (a) J. Buckle, P. G. Harrison, T. J. King and J. A. Richards, J. Chem. Soc., Chem. Commun., 1972, 1104;
26. (b) J. Buckle and P. G. Harrison, J. Organomet. Chem., 1973, 49, C17.
27. (a) G. Matsubayashi, I. Kawafune, T. Tanaka, S. Nishigaki and K. Nakatsu, J. Organomet. Chem., 1980, 187, 113;
28. (b) I. Kawafune and G. Mastubayashi, Inorg. Chim. Acta, 1983, 70, 1.
29. J. A. Albanese, D. L. Staley, A. L. Rheingold and J. L. Burmeister, Inorg. Chem., 1990, 29, 2209.
30. G. Facchin, L. Zanotto, R. Bertani, L. Canovese and P. Uguagliati, J. Chem. Soc., Dalton Trans., 1993, 2871.
31. L. R. Falvello, S. Fernández, R. Navarro and E. P. Urriolabeitia, Inorg. Chem., 1996, 35, 3064.
32. U. Belluco, R. A. Michelin, R. Bertani, G. Facchin, G. Pace, L. Zanotto, M. Mozzon, M. Furlan and E. Zangrando, Inorg. Chim. Acta, 1996, 252, 355.
33. L. R. Falvello, S. Fernández, R. Navarro, I. Pascual and E. P. Urriolabeitia, J. Chem. Soc., Dalton Trans., 1997, 763.
34. L. R. Falvello, S. Fernández, R. Navarro and E. P. Urriolabeitia, Inorg. Chem., 1997, 36, 1136.
35. I. C. Barco, L. R. Falvello, S. Fernández, R. Navarro and E. P. Urriolabeitia, J. Chem. Soc., Dalton Trans., 1998, 1699.
36. S. Fernández, M. M. García, R. Navarro and E. P. Urriolabeitia, J. Organomet. Chem., 1998, 561, 67.
37. D. Soulivong, C. Wieser, M. Marcellin, D. Matt, A. Harriman and L. Toupet, J. Chem. Soc., Dalton Trans., 1997, 2257.
38. L. R. Falvello, M. M. García, I. Lázaro, R. Navarro and E. P. Urriolabeitia, New. J. Chem., 1999, 23, 227.
39. L. R. Falvello, S. Fernández, R. Navarro and E. P. Urriolabeitia, New J. Chem., 1997, 21, 909.
40. E. Díez-Barra, J. Fernández-Baeza, M. M. Kubicki, A. Lara-Sánchez, A. Otero, N. Poujaud and J. Tejeda, J. Organomet. Chem., 1997, 542, 291.
41. A. Antiñolo, F. Carrillo-Hermosilla, E. Díez-Barra, J. Fernández-Baeza, A. Lara-Sánchez, A. Otero and J. Tejeda, J. Organomet. Chem., 1998, 570, 97.
42. For recent papers concerning ylides acting as polydentate ligands see, for instance: E. J. Fernández, M. C. Gimeno, A. Laguna, J. M. López-de-Luzuriaga and Elena Olmos, Polyhedron, 1998, 17, 3919 and references therein;
43. J. Vicente, M. T. Chicote, M. C. Lagunas, P. G. Jones and B. Ahrens, Inorg. Chem., 1997, 36, 4938 and references therein;
44. M. C. Gimeno, P. G. Jones, A. Laguna, M. Laguna and I. Lázaro, J. Chem. Soc., Dalton Trans., 1993, 2223.
45. M. C. Gimeno, P. G. Jones, A. Laguna and M. D. Villacampa, J. Chem. Soc., Dalton Trans., 1995, 805 and references therein.
46. (a) R. G. Pearson, J. Chem. Educ., 1968, 45, 581;
47. R. G. Pearson, J. Chem. Educ., 1968, 45, 643;
48. (b) R. G. Pearson, J. Am. Chem. Soc., 1963, 85, 3533;
49. (c) R. G. Pearson, Science, 1966, 151, 172;
50. (d) R. G. Pearson, Chem. Br., 1967, 3, 103.
51. J. A. Davies and F. R. Hartley, Chem. Rev., 1981, 81, 79 and references therein.
52. For the theoretical treatment of the HSAB rules see: G. Klopman, J. Am. Chem. Soc., 1968, 90, 223.
53. C. K. Jørgensen, Inorg. Chem., 1964, 3, 1201.
54. R. G. Pearson, Inorg. Chem., 1973, 12, 712.
55. Selected references: (a) G. R. Clark and G. J. Palenik, Inorg. Chem., 1970, 9, 2754;
56. (b) J. Dehand, J. Jordanov, M. Pfeffer and M. Zinsius, C. R. Acad. Sci. Paris, Serie C, 1975, 281, 651;
57. (c) M. Pfeffer, D. Grandjean and G. Le Borgne, Inorg. Chem., 1981, 20, 4426;
58. (d) C. Arlen, M. Pfeffer, O. Bars and G. Le Borgne, J. Chem. Soc., Dalton Trans., 1986, 359;
59. (e) J. Vicente, M. D. Bermúdez, F. J. Carrión and P. G. Jones, J. Organomet. Chem., 1996, 508, 53;
60. (f) R. J. Puddephatt, in Comprehensive Organometallic Chemistry I, E. W. Abel, F. G. A. Stone and G. Wilkinson, Eds., Pergamon Press, Oxford, 1982, Vol. 2, p. 789;
61. (g) J. Vicente, J. A. Abad, A. D. Frankland and M. C. Ramírez de Arellano, Chem. Commun., 1997, 959.
62. J. Vicente, A. Arcas, D. Bautista and P. G. Jones, Organometallics, 1997, 16, 2127.
63. A. J. Deeming, I. P. Rothwell, M. B. Hursthouse and L. New, J. Chem. Soc., Dalton Trans., 1978, 1490.
64. (a) B. L. Booth and K. G. Smith, J. Organomet. Chem., 1981, 220, 229;
65. (b) H. Schmidbaur, T. Costa and B. Milewski-Mahrla, Chem. Ber., 1981, 114, 1428;
66. (c) H. Schmidbaur, T. Costa, B. Milewski-Mahrla, F. H. Köhler, Y.-H. Tsay, C. Krüger, J. Abart and F. E. Wagner, Organometallics, 1982, 1, 1266.
67. (a) J. Vicente, M. T. Chicote, I. Sauras-Llamas and P. G. Jones, Organometallics, 1989, 8, 767;
68. (b) J. Vicente, M. T. Chicote and I. Sauras-Llamas, J. Chem. Soc., Dalton Trans., 1990, 1941;
69. (c) J. Vicente, M. T. Chicote, I. Sauras-Llamas, M. J. López-Muñoz and P. G. Jones, J. Chem. Soc., Dalton Trans., 1990, 3683.
70. R. Sanehi, R. K. Bansal and R. C. Mehrotra, J. Organomet. Chem., 1986, 303, 351.
71. J. Vicente, M. T. Chicote, I. Sauras-Llamas, P. G. Jones, K. Meyer-Bäse and C. F. Erdbrügger, Organometallics, 1988, 7, 997.
72. (a) J. A. Ford and C. V. Wilson, J. Org. Chem., 1961, 26, 1433;
73. (b) D. B. Deeney and J. Song, J. Org. Chem., 1964, 29, 495.
74. L. R. Falvello, S. Fernández, R. Navarro, A. Rueda and E. P. Urriolabeitia, Inorg. Chem., 1998, 37, 6007.
75. (a) D. A. Clarke, R. D. W. Kemmitt, M. A. Mazid, P. McKenna, D. R. Russell, M. D. Schilling and L. J. S. Sherry, J. Chem. Soc., Dalton Trans., 1984, 1993;
76. (b) R. D. W. Kemmitt, P. McKenna, D. R. Russell and L. J. S. Sherry, J. Chem. Soc., Dalton Trans., 1985, 259;
77. (c) A. Imran, R. D. W. Kemmitt, A. J. W. Markwick, P. McKenna, D. R. Russell and L. J. S. Sherry, J. Chem. Soc., Dalton Trans., 1985, 549;
78. (d) K. W. Chiu, W. Henderson, R. D. W. Kemmitt and L. J. S. Prouse, J. Chem. Soc., Dalton Trans., 1988, 427;
79. (e) R. D. W. Kemmitt, P. McKenna, D. R. Russell and L. J. S. Prouse, J. Chem. Soc., Dalton Trans., 1989, 345.
80. Some representative examples: (a) J. C. Baldwin and W. C. Kaska, Inorg. Chem., 1979, 18, 686;
81. (b) M. L. Illingsworth, J. A. Teagle, J. L. Burmeister, W. C. Fultz and A. L. Rheingold, Organometallics, 1983, 2, 1364;
82. (c) J. A. Teagle and J. L. Burmeister, Inorg. Chim. Acta, 1986, 118, 65;
83. (d) J. Vicente, M. T. Chicote and J. Fernández-Baeza, J. Organomet. Chem., 1989, 364, 407;
84. (e) A. J. Deeming, D. Nuel, N. I. Powell and C. Whittaker, J. Chem. Soc., Dalton Trans., 1992, 757;
85. (f) D. Heineke, D. Scott Bohle and H. Vahrenkamp, Chem. Ber., 1993, 126, 355;
86. (g) D. Heineke and H. Vahrenkamp, Chem. Ber., 1993, 126, 365;
87. (h) J. Vicente, M. T. Chicote, M. C. Lagunas, P. G. Jones and E. Bembenek, Organometallics, 1994, 13, 1243;
88. (i) J. Vicente, M. T. Chicote, M. C. Lagunas and P. G. Jones, Inorg. Chem., 1995, 34, 5441;
89. (j) G. Facchin, L. Zanotto, R. Bertani and G. Nardin, Inorg. Chim. Acta, 1996, 245, 157;
90. (k) M. Steiner, H. Grützmacher, H. Prtizkow and L. Zsolnai, Chem. Commun., 1998, 285;
91. (l) S. Wingerter, H. Gornitzka, G. Bertrand and D. Stalke, Eur. J. Inorg. Chem., 1999, 173.
92. L. R. Falvello, S. Fernández, R. Navarro, A. Rueda and E. P. Urriolabeitia, Organometallics, 1998, 17, 5887.
93. See for instance: L. R. Falvello, J. Forniés, R. Navarro, A. Rueda and E. P. Urriolabeitia, Organometallics, 1996, 15, 309.
94. See for instance: (a) W. Oberhauser, C. Bachmann, T. Stampfl, R. Haid and P. Brüggeller, Polyhedron, 1997, 16, 2827;
95. (b) B. Wu, W. Zhang, X. Huang, X. Wu and S. Yu, Polyhedron, 1997, 16, 801.
96. L. R. Falvello, S. Fernández, R. Navarro and E. P. Urriolabeitia, Inorg. Chem., 1999, 38, 2455.